Antimalarial (+)-trans-hexahydrodibenzopyran derivatives from Machaerium multiflorum.

Bioassay-guided fractionation of Machaerium multiflorum yielded the hitherto unreported (+)-trans-hexahydrodibenzopyrans machaeriol A (1) and machaeriol B (2), as well as the known guaiane sesquiterpene (-)-kessane. Structure elucidation was based on (1)H and (13)C NMR data, mainly 2D NMR (1)H-(1)H COSY, (1)H-(13)C HMQC, (1)H-(13)C HMBC, and (1)H-(1)H NOESY experiments. This is the first report of the hexahydrodibenzopyrans from a higher plant other than the genus Cannabis. The cannabimimetic activity was thus evaluated by radioligand binding assay for cannabinoid receptor CB1, which indicated, notably, that both 1 and 2 were inactive. In addition, the cross reactivity of 1 and 2 toward antibodies designed for urinary metabolites of cannabinoids was evaluated with the EMIT and On Line cannabinoids assays. Both compounds showed no response at 100 000 ng/mL in both assays. Machaeriol B (2) demonstrated in vitro antimalarial activity (IC(50) = 120 ng/mL) against Plasmodium falciparum W-2 clone.

Coca paste: chemical analysis and smoking experiments.

Several samples of Colombian and a sample of Peruvian coca paste were subjected to chemical analysis to ascertain the complexity of these products. A neutral and acid fraction and a basic fraction were analyzed by gas chromatography/flame ionization detection (GC/FID) and gas chromatography/mass spectrometry (GC/MS). The basic fraction was also analyzed as its trimethylsilyl (TMS) derivative. Several gasoline residue components were identified in the neutral fraction. In addition to cocaine (greater than 60% in all cases), other alkaloids were identified. Lead and manganese analyses were carried out on these samples. While all the samples contained no lead (less than 45 ppm), most of the Colombian samples contained significant amounts of manganese (greater than 5%). Preliminary smoking experiments with a Colombian coca paste sample indicated that it behaves more like free cocaine than like a cocaine sulfate salt.

Chromatographic and spectroscopic profiles of Cannabis of different origins: Part I.

High-resolution capillary gas chromatography with flame ionization detection and mass spectrometry (GC and GC/MS) and high-performance liquid chromatography (HPLC) were used to establish complex chemical profiles (chemical signatures) of Cannabis samples of known origin. Over 100 compounds could be differentiated, including noncannabinoids (terpenes, alkanes) as well as minor and major cannabinoids and their acids. A characteristic peak pattern was found within a limited number of specimens of identical origin. Correlation studies on the basis of peak area ratios [A(x)/A(i.s.)] showed the feasibility of tracing Cannabis chemically to its country of origin. Several forensic science applications for the chromatographic and spectroscopic profiles of confiscated Cannabis samples are discussed, such as detection of additives (phencyclidine), differentiation of chemotypes, and monitoring of tetrahydrocannabinol (THC) potency.

Chromatographic and spectroscopic profiles of Cannabis of different origins: Part I

High-resolutin capillary gas chromatography with flame ionization detection and mass spectrometry (GC and GC/MS) and high-performance liquid chromatography (HPLC) were used to establish complex chemical profiles (chemical signatures) of Cannabis samples of known origin. Over 100 compounds could be differentiated, including noncannabinoid (terpenes, alkanes) as well as minor and major cannabinoids and their acids. A characteristic peak pattern was found within a limited number of specimens of identical origin. Correlation studies on the basis of peak area ratios(A(x)/A(i.s.)) showed the feasibility of tracing Cannabis chemically to its country of origin. Several forensic science applications for the chromatography and spectroscopic profiles of confiscated Cannabis samples are discussed, such as detection of additive (phencyclidine),differentiation of chemotypes, and monitoring of tetrhydrocannabinol (THC) potency. (AU)

Constituents of Cannabis sativa, XXV. Isolation of two new dihydrostilbenes from a Panamanian variant.

Two new dihydrostilbene compounds (named cannabistilbenes I and II) were isolated from a polar acidic fraction of a Panamanian variant of Cannabis sativa grown in Mississippi. The structure of cannabistilbene I was shown to be 3,4'-dihydroxy-5-methoxy-3'-(3-methylbut-2-enyl)-dihydrostilben e (1) from spectral data which was confirmed by synthesis. There is spectral evidence to indicate that cannabistilbene II could be represented by either structure 3 or 4.

Constituents in Erythroxylum coca I: gas chromatographic analysis of cocaine from three locations in Peru.

A method for the determination of cocaine content in coca leaves (Erythroxylum coca) has been developed. The procedure involves refluxing the powdered leaves in 95% ethanol for 15 minutes, followed by acid-base partitioning with chloroform and a GLC assay. The recovery of cocaine was quantitative. This procedure was applied to determine cocaine content in three samples of Erythroxylum coca Lam. collected from different geographic locations in Peru. Using androst-4-ene-3,17-dione as the internal standard the calibration curve was linear over a factor of 0.5 to 10 fold cocaine concentration relative to internal standard. The slope (b) was 0.733, the coefficient of determination (r2) was 1.00 and the average precision was 3.9%.

Detection and analysis of paraquat in confiscated marijuana samples.

A spectrophotometric method used to test for paraquat in 160 confiscated marijuana samples is described. Twenty of these samples (12.5 per cent) tested positive for paraquat. Nine confiscated hash oil samples tested negative. The identification of paraquat was proven by isolation, chromatography, and spectral methods. The cannabinoids in paraquat positive Cannabis samples were analysed.